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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Southwest Side bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (487)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is 3.475.692 ₫
4.079.988 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (189)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is 6.597.495 ₫
7.447.913 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is 1.116.434 ₫
2.232.342 ₫ total
includes taxes & fees
18 Jan - 19 Jan 2026
Dorothy's
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497)
"Nice shared spaces"
United States
Erica
The price is 2.392.171 ₫
4.367.259 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
House 5863 - Chicago Bed and Breakfast
Exterior
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (627)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is 947.916 ₫
2.165.999 ₫ total
includes taxes & fees
28 Dec - 29 Dec
The Villa Toscana
Lobby sitting area
Villa D' Citta

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113)
"Great place"
United States
Jeffrey
The price is 5.420.236 ₫
6.362.886 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (121)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is 6.082.461 ₫
6.750.215 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Harvey House Bed & Breakfast
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (383)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is 4.151.609 ₫
4.686.655 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Ray's Bucktown B&B
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"I prefer Embassy Suite over any hotel. ES does not fail in quality, comfort, cleanliness. We enjoyed Chicago very much. Embassy Suite was in walking distance. Staff were very friendly. "
Chastity 3-night trip
Posted 11 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
2,549
Accommodation
9 B&B
Lowest Price
2.165.999 ₫
Highest Price
7.447.913 ₫